BI
Brightway InsuranceSales Representative – 1099 Contractor
Sales Representative selling personal and commercial lines for Brightway Insurance. Generating leads and hitting sales targets while providing tailored insurance solutions to clients.
About the role
- Own and exceed your quota by closing new logo deals with employers of 7,500+ employees, selling high-ACV (Six and Seven-Figure) multi-product contracts.
- Manage full-cycle enterprise sales processes including outbound prospecting, discovery, consultative pitching, product demonstration, proposal development, negotiation, and close.
- Cultivate trusted relationships with senior leaders across Human Resources, Total Rewards, Benefits, and People teams to deeply understand organizational needs and priorities.
- Collaborate closely with Account Development Executives (BDRs), Consultant Relations, and Marketing to build pipeline and support coordinated regional go-to-market efforts.
- Partner with key benefits consultants, brokers, and channel partners to amplify market reach and co-sell effectively.
- Serve as a strategic expert in the mental health benefits space, leveraging industry trends, buyer insights, and competitive dynamics to shape your sales approach.
- Identify and propose strategic approaches to technical sales challenges affecting the enterprise team, establish sales standards, and drive adoption of solution-based selling methodologies.
- Provide accurate forecasting and pipeline reporting to support revenue planning and team-wide accountability.
- Partner with Sales Ops and leadership to refine and implement sales excellence processes that support consistency across enterprise deals.
- Identify market trends and propose innovative solutions in collaboration with cross-functional teams to support long-term business opportunities.
- Represent Headspace at high-impact industry events and conferences to enhance brand presence and cultivate new enterprise relationships.
- Contribute to organizational capability building by identifying skill gaps, providing mentorship, and creating development opportunities for other team members to enhance overall sales effectiveness.
- Support capability-building across the team by sharing best practices, mentoring peers, and contributing to learning opportunities.
- Travel as needed (~30%) to advance key deals and attend in-person meetings or events.
Requirements
- 8+ years of experience in enterprise, digital health, or benefits solution sales with a strong track record of exceeding quotas.
- Proven ability to sell complex solutions into HR/Benefits departments at large employers, ideally with deal sizes over $500,000 in annual contract value.
- Deep understanding of the U.S. employer benefits ecosystem, including mental health, employee assistance programs (EAP), and wellbeing trends.
- Strong consultative selling, negotiation, and executive presence with the ability to navigate long and strategic sales cycles.
- Ability to manage multiple stakeholders, including HR, Finance, Procurement, and external brokers/consultants.
- Demonstrated ability to identify process gaps and implement improved sales methodologies that enhance team effectiveness and customer outcomes.
- Experience applying design thinking principles to sales challenges, with the ability to challenge assumptions and continuously improve sales approaches.
- Excellent communication skills—both written and verbal—and comfort developing business cases and delivering compelling presentations.
- Highly self-motivated, organized, and goal-oriented with a bias for action in a fast-paced, high-growth environment.
- Comfortable using CRM tools like Salesforce to manage pipeline and forecast accurately.
Benefits
- base salary
- stock awards
- comprehensive healthcare coverage
- monthly wellness stipend
- retirement savings match
- lifetime Headspace membership
- generous parental leave
Job title
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Experience level
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Degree requirement
No Education Requirement
Location requirements
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